Sodium Hydroxide → HCID 66897999, compound

HRID 1188932Notes

Reaction equation

HRID 1188932 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([O:17][C:18]2[CH:19]=[N:20][C:21]([CH2:24][O:25][CH3:26])=[CH:22][CH:23]=2)[CH:6]=[C:7]2[C:11]=1[NH:10][C:9]([C:12]([O:14]CC)=[O:13])=[CH:8]2.[OH-].[Na+]>O1CCCC1.C(O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([O:17][C:18]2[CH:19]=[N:20][C:21]([CH2:24][O:25][CH3:26])=[CH:22][CH:23]=2)[CH:6]=[C:7]2[C:11]=1[NH:10][C:9]([C:12]([OH:14])=[O:13])=[CH:8]2

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 58237114HCID 58237114, compound

Product 1

HCID 66897999HCID 66897999, compoundYield 103.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of ethyl 7-methoxy-5-{[6-(methoxymethyl)pyridin-3-yl]oxy}-1H-indole-2-carboxylate (2.39 g) in a mixture of tetrahydrofuran (15 mL) and ethanol (10 mL) was added 1M aqueous sodium hydroxide solution (10 mL), and the mixture was stirred at 50° C. for 1 h. The mixture was concentrated under reduced pressure. The residue was dissolved in water, and 1M hydrochloric acid (10 mL) was added to the mixture. The mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over magnesium sulfate, filtered and concentrated to give the title compound (2.28 g, 100%) as a pale yellow amorphous solid. MS 329 (MH+).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. dissolutionThe residue was dissolved in water
  3. addition1M hydrochloric acid (10 mL) was added to the mixture
  4. extractionThe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-50313a46d5cc43ffb0ccf85c5bffd355
Source dataset
uspto-grants-2014_03
Patent number
US08673942B2

Reaction notes

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